Fife Symington holds a degree in Dutch art history from Harvard University and has a background in real estate development. He founded The Symington Company, where he developed notable projects such as the Esplanade and the Mercado. Symington's professional experience includes serving in the United States Air Force during the Vietnam War, where he was awarded the Bronze Star. He also held a position on the Southwest Savings and Loan Association board of directors.

Fife Symington's political philosophy is rooted in a Hayekian vision of limited government and free markets, yet his personal financial struggles in real estate development reveal a complex tension between ideology and practice. Symington's strategic approach often merges free-market principles with a pragmatic need to navigate economic downturns, raising questions about the consistency of his ideological stance. His rhetorical style tends to emphasize the virtues of free enterprise while skirting the implications of his own financial failures.